Triethylamine → HCID 22591868, compound

HRID 22905Notes

Reaction equation

HRID 22905 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]([O:16]CC3C=CC=CC=3)=[O:15])[CH:8]=2)[CH2:5][CH:4]([C:24]([NH:26][CH:27]([C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:25])[CH2:3]1.C(N(CC)CC)C>CO.[Pd]>[CH2:32]([O:31][C:29]([CH2:28][CH:27]([NH:26][C:24]([CH:4]1[CH2:5][N:6]([C:7]2[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)[C:2](=[O:1])[CH2:3]1)=[O:25])[C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)=[O:30])[CH3:33]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 22591795HCID 22591795, compound

Product 1

HCID 22591868HCID 22591868, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-{(5-oxo-1-(3-{(benzyloxycarbonyl)methyl}phenyl)pyrrolidin-3-yl)carbonylamino}-3-(3-pyridyl)propanoate (2.6 g, 5.0 mmol, 1.0 eq), triethylamine (1.5 mL) in methanol (20 mL), was added 10% Pd/C (Aldrich, 0.5 g, 0.5 mmol, 0.1 eq). Hydrogenation was carried out under a pressure of 1 atm. After stirring for 5 hours, the catalyst was filtered through a pad of celite and the filtrate was concentrated with rotary evaporator. The title compound was obtained as an off-white solid. MS (ES+): 440 (M+H)+; (ES−): 438 (M−H)−.

Workup

  1. filtrationthe catalyst was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated with rotary evaporator

Sources & evidence

ORD record
ord-e50d272e54184c64ac2edbce5ca93a73
Source dataset
uspto-grants-2005_02
Patent number
US06849639B2

Reaction notes

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